Skip to main content
SpringerLink
Log in

Inhibitory effect of glucodistylin from the bark of Quercus acutissima on human recombinant aldose reductase and sorbitol accumulation

  • Research Articles
  • Drug Discovery and Development
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

A flavanol glycoside, glucodistylin (1) and three polyphenol derivatives, gallate (2), (+)-catechin (3) and (+)-gallocatechin (4) were isolated from an aqueous acetone extract of the bark of Quercus acutissima. Of these compounds, glucodistylin exhibited uncompetitive inhibitory activity against recombinant human aldose reductase with an IC50 value of 7.2 μM. Furthermore, glucodistylin inhibited sorbitol accumulation by 48.84% at 50 μM. This flavonoid showed therapeutic potential in the prevention and treatment of diabetes-related complications.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Reference

  • Asano, T., Saito, Y., Kawakami, M., Yamada, N., Sekino, H., and Hasegawa, S., Erythrocytic sorbitol contents in diabetic patients correlate with blood aldose reductase protein contents and plasma glucose levels, and are normalized by the potent aldose reductase inhibitor fidarestat (SNK-860). J. Diabetes Complications, 18, 336–342 (2004).

    Article  PubMed  Google Scholar 

  • Crabbe, M. J. and Goode, D., Aldose reductase: a window to the treatment of diabetic complications? Prog. Retin. Eye Res., 17, 313–383 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Dübeler, A., Voltmer, G., Gora, V., Lunderstädt, J., and Zeeck, A., Phenols from Fagus sylvatica and their role in defence against Cryptococcus fagisuga. Phytochemistry, 45, 51–57 (1997).

    Article  Google Scholar 

  • Gabbay, K. H., The sorbitol pathway and the complications of diabetes. N. Engl. J. Med., 288, 831–836 (1973).

    Article  PubMed  CAS  Google Scholar 

  • Haraguchi, H., Ohmi, I., Masuda, H., Tamura, Y., Mizutani, K., Tanaka, O., and Chou, W. H., Inhibition of aldose reductase by dihydroflavonols in Engelhardtia chrysolepis and effects on other enzymes. Experientia, 52, 564–567 (1996).

    Article  PubMed  CAS  Google Scholar 

  • Haraguchi, H., Ohmi, I., Fukuda, A., Tamura, Y., Mizutani, K., Tanaka, O., and Chou, W. H., Inhibition of aldose reductase and sorbitol accumulation by astilbin and taxifolin dihydroflavonols in Engelhardtia chrysolepis. Biosci. Biotechnol. Biochem., 61, 651–654 (1997).

    Article  PubMed  CAS  Google Scholar 

  • Hayman, S. and Kinoshita, J. H., Isolation and properties of lens aldose reductase. J. Biol. Chem., 240, 877–882 (1965).

    PubMed  CAS  Google Scholar 

  • Ishimaru, K., Nonaka, G., and Nishioka, I., Phenolic glucoside gallates from Quercus mongolica and Q. acutissima. Phytochemistry, 26, 1147–1152 (1987).

    Article  CAS  Google Scholar 

  • Kador, P. F., The role of aldose reductase in the development of diabetic complications. Med. Res. Rev., 8, 325–352 (1988).

    Article  PubMed  CAS  Google Scholar 

  • Kwang-Hyok, S., Ui-Nam, P., Sarkar, C., and Bhadra, R., A sensitive assay of red blood cell sorbitol level by high performance liquid chromatography: potential for diagnostic evaluation of diabetes. Clin. Chim. Acta, 354, 41–47 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Lee, Y. S., Kang, Y. H., Jung, J. Y., Kang, I. J., Han, S. N., Chung, J. S., Shin, H. K., and Lim, S. S., Inhibitory constituents of aldose reductase in the fruiting body of Phellinus linteus. Biol. Pharm. Bull., 31, 765–768 (2008).

    Article  PubMed  CAS  Google Scholar 

  • Malone, J. I., Knox, G., Benford, S., and Tedesco, T. A., Red blood cell sorbitol: an indicator of diabetic control. Diabetes, 29, 861–864 (1980).

    Article  PubMed  CAS  Google Scholar 

  • Malone, J. I., Leavengood, H., Peterson, M. J., O’Brien, M. M., Page, M. G., and Aldinger, C. E., Red blood cell sorbitol as an indicator of polyol pathway activity. Inhibition by sorbinil in insulin-dependent diabetic subjects. Diabetes, 33, 45–49 (1984).

    Article  PubMed  CAS  Google Scholar 

  • Matsuda, H., Morikawa, T., Toguchida, I., and Yoshikawa, M., Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem. Pharm. Bull., 50, 788–795 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Nishimura, H., Nonaka, G., and Nishioka, I., A gallotannin and two ellagitannins containing a p-hydroxyphenethyl alcohol 1-O-β-D-glucoside (salidroside) core from Quercus stenophylla Makino. Chem. Pharm. Bull., 32, 1735–1740 (1984a).

    CAS  Google Scholar 

  • Nishimura, H., Nonaka, G., and Nishioka, I., Tannins and related compounds. XIX. Eight new gallotannins containing a protoquercitol core from Quercus stenophylla Makino. Chem. Pharm. Bull., 32, 1741–1749 (1984b).

    CAS  Google Scholar 

  • Nonaka, G., Nishimura, H., and Nishioka, I., Seven new phenol glucoside gallates from Quercus stenophylla Makino. Chem. Pharm. Bull., 30, 2061–2067 (1982).

    CAS  Google Scholar 

  • Nonaka, G., Nishimura, H., and Nishioka, I., Isolation and structures of stenophyllanins A, B, and C, novel tannins from Quercus stenophylla Makino. J. Chem. Soc., 33, 163–172 (1985).

    Google Scholar 

  • Sakushima, A., Ohno, K., Coskun, M., Seki, K.-I., and Ohkura, K., Separation and Identification of Taxifolin 3-O-Glucoside Isomers from Chamaecyparis Obtusa (Cupressaceae). Nat. Prod. Res., 16, 383–387 (2002).

    Article  CAS  Google Scholar 

  • Saraswat, M., Muthenna, P., Suryanarayana, P., Petrash, J. M., and Reddy, G. B., Dietary sources of aldose reductase inhibitors: prospects for alleviating diabetic complications. Asia Pac. J. Clin. Nutr., 17, 558–565 (2008).

    PubMed  Google Scholar 

  • Shimizu, M., Terashima, T. I. S., Hayashi, T., Arisawa, M., Morita, N., Kurokawa, S., Ito, K., and Hashimoto, Y., Inhibition of lens aldose reductase by flavonoids. Phytochemistry, 23, 1885–1888 (1984).

    Article  CAS  Google Scholar 

  • Shinohara, R., Ohta, Y., Yamauchi, M., and Ishiguro, I., Improved fluorometric enzymatic sorbitol assay in human blood. Clin. Chim. Acta, 273, 171–184 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Suzen, S. and Buyukbingol, E., Recent studies of aldose reductase enzyme inhibition for diabetic complications. Curr. Med. Chem., 10, 1329–1352 (2003).

    Article  PubMed  CAS  Google Scholar 

  • Tanaka, N., Shimomura, K., and Ishimaru, K., Tannin productin in callus cultures of Quercus acutissima. Phytochemistry, 40, 1151–1154 (1995).

    Article  CAS  Google Scholar 

  • Ueda, H., Kawanishi, K., and Moriyasu, M., Effects of ellagic acid and 2-(2,3,6-trihydroxy-4-carboxyphenyl) ellagic acid on sorbitol accumulation in vitro and in vivo. Biol. Pharm. Bull., 27, 1584–1587 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Vertommen, J., Rillaerts, E., Gysels, M., and De Leeuw, I., Erythrocyte sorbitol content in diabetic patients: relation to metabolic control. Diabete Metab., 13, 182–186 (1987).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Center for Efficacy Assessment and Development of Functional Foods and Drugs, Hallym University, Chuncheon, 200-702, Korea

    Yeon Sil Lee & Soon Sung Lim

  2. Institute of Natural Medicine, Hallym University, Chuncheon, 200-702, Korea

    Jin Kyu Kim, Moo-Ho Won & Soon Sung Lim

  3. Departement of Forest Biomaterials Engineering, Kangwon National University, Chuncheon, 200-701, Korea

    Young Soo Bae

  4. Department of Anatomy and Neurobiology, Hallym Univertisy, Chuncheon, 200-701, Korea

    Moo-Ho Won

  5. Department of Food Science and Nutrition, Hallym University, Chuncheon, 200-702, Korea

    Il-Jun Kang & Soon Sung Lim

Authors
  1. Yeon Sil Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jin Kyu Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Young Soo Bae
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Moo-Ho Won
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Il-Jun Kang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Soon Sung Lim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Soon Sung Lim.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lee, Y.S., Kim, J.K., Bae, Y.S. et al. Inhibitory effect of glucodistylin from the bark of Quercus acutissima on human recombinant aldose reductase and sorbitol accumulation. Arch. Pharm. Res. 34, 211–215 (2011). https://doi.org/10.1007/s12272-011-0205-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-011-0205-1

Key words

Search

Navigation